Title: The Best Ashland, WI Chalets from $394 | Expedia.com [Ashland Travel Guide](https://expedia.com/Ashland.dx6170)[Hotels in Ashland](https://expedia.com/Ashland-Hotels.d6170.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.com/Ashland-Vacation-Rentals.d6170.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.com/Cheap-Flights-To-Ashland.d6170.Travel-Guide-Flights)[Car Rentals in Ashland](https://expedia.com/Car-Rentals-In-Ashland.d6170.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.com/Ashland.d6170.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ashland chalets ![Interior](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/5f4f1c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/329b92a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/46d0584d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/7727397e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Bayfield [](https://www.expedia.com/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.Hotel-Information) 9.8/10 Exceptional (59 reviews) "Beautiful private peaceful cabin. We thoroughly enjoyed our visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacie G. $349 nightly $394 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/6cbacc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/0d8b867d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/85059b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/088b9f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Bayfield [](https://www.expedia.com/Bayfield-Hotels-Northwoods-Chalet-Brickyard-Creek.h39174175.Hotel-Information) 10/10 Exceptional (78 reviews) "Beautiful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan S. $361 nightly $408 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Bayfield-Hotels-Northwoods-Chalet-Brickyard-Creek.h39174175.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/15d9d869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/bd3af196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/d5285d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/bb6d11bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Upson [](https://www.expedia.com/Upson-Hotels-Spacious-9-Bedroom-Chalet-With-WiFi-And-AC-In-Delightful-Upson-Floor-2.h108775240.Hotel-Information) 10/10 Exceptional (1 review) "A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy H. $1,627 nightly $1,716 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Upson-Hotels-Spacious-9-Bedroom-Chalet-With-WiFi-And-AC-In-Delightful-Upson-Floor-2.h108775240.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16®ionId=6170&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6170) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CHALET) Apartments [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APARTMENT) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FAshland-Chalets.d6170-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FAshland-Chalets.d6170-aaChalets.Travel-Guide-Accommodation) ## Top Ashland Hotel Reviews ![Best Western The Hotel Chequamegon](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/2ca0a607_y.jpg) ### Best Western The Hotel Chequamegon 10/10 Excellent "I loved this place, perfect combination of modern and old charm. The room was huge and comfortable with a great view of frozen Lake Superior. " [](https://expedia.com/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.Hotel-Information) ![Blue Wave Inn](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/198db952_y.jpg) ### Blue Wave Inn 10/10 Excellent "Beautiful, well-appointed, and unique room!" [](https://expedia.com/Ashland-Hotels-Blue-Wave-Inn.h26680614.Hotel-Information) ![The Washburn Inn - On the Lake](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/b643ecc7_y.jpg) ### The Washburn Inn - On the Lake 10/10 Excellent "The staff members were very helpful and accommodating. The rooms are newly renovated, with comfortable beds. Hot and fresh locally sourced coffee was great to start the day with!" [](https://expedia.com/Washburn-Hotels-The-Washburn-Inn-On-The-Lake.h459665.Hotel-Information) ![Cobblestone Inn & Suites - Ashland](https://images.trvl-media.com/lodging/28000000/27290000/27288700/27288622/15c117bb_y.jpg) ### Cobblestone Inn & Suites - Ashland 10/10 Excellent "great" [](https://expedia.com/Ashland-Hotels-Cobblestone-Inn-Suites-Ashland.h27288622.Hotel-Information) ![Days Inn by Wyndham Hurley](https://images.trvl-media.com/lodging/1000000/30000/25400/25374/cfe634fe_y.jpg) ### Days Inn by Wyndham Hurley 10/10 Excellent "Great staff great rooms" [](https://expedia.com/Hurley-Hotels-Days-Inn-By-Wyndham-Hurley.h25374.Hotel-Information) ![Super 8 by Wyndham Ashland](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/23163c47_y.jpg) ### Super 8 by Wyndham Ashland 10/10 Excellent "Location" [](https://expedia.com/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.Hotel-Information) ![Legendary Waters Resort & Casino](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/00893773_y.jpg) ### Legendary Waters Resort & Casino 10/10 Excellent "Great one night stay. Room was clean, quiet and comfortable. " [](https://expedia.com/Bayfield-Hotels-Legendary-Waters-Resort-Casino.h61478483.Hotel-Information) ![Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows ](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/27c92375_y.jpg) ### Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows 10/10 Excellent "Host was great!!! Very responsive to the questions asked. Would definitely stay there again " [](https://expedia.com/Bayfield-Hotels-Apostle-Iss-Gatewaynext-Scenic-Marinasfireplacejacuzzicorner-W-4-Windows.h53620159.Hotel-Information) ![Cedars Motel](https://images.trvl-media.com/lodging/18000000/17280000/17270400/17270312/b658fa50_y.jpg) ### Cedars Motel 10/10 Excellent "It was our second stay at Cedars and we’ll absolutely be back. 10/10 would recommend." [](https://expedia.com/Ironwood-Hotels-Cedars-Motel.h17270312.Hotel-Information) ## Find out more about Ashland ## Ashland Chalets information | Number of reviews | 138 | | ----------------- | ---------- | | Accommodation | 15 Chalets | | Lowest Price | $394 | | Highest Price | $1,716 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Ashland Historical Museum ](https://www.expedia.com/Ashland-Historical-Museum-Hotels.0-l6323159-0.Travel-Guide-Filter-Hotels) - [Hotels near Chequamegon Bay Golf Course ](https://www.expedia.com/Chequamegon-Bay-Golf-Course-Hotels.0-l6323167-0.Travel-Guide-Filter-Hotels) - [Hotels near John F. 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